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Income Taxes - Tax Effects of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($)
$ in Millions
Dec. 31, 2022
Dec. 31, 2021
Income Tax Disclosure [Abstract]    
Operating loss carryforwards $ 167.6 $ 170.2
Capital loss carryforwards 6.7 0.3
Insurance reserves: Losses and loss adjustment expenses 28.3 16.7
Unrealized losses on investments 20.6 0.0
Accrued expenses 6.1 4.6
Foreign tax credit carryforwards 19.8 20.2
Unearned premiums 36.0 28.3
Intangible assets 0.7 0.0
Office properties and equipment 14.2 15.1
Operating lease liability 18.5 19.2
Other temporary differences 3.7 2.9
Total deferred tax assets 322.2 277.5
Less valuation allowance (145.7) (225.9)
Deferred tax assets, net of valuation allowance 176.5 51.6
Unrealized (gains) on investments 0.0 (2.5)
Intangible assets 0.0 (2.8)
Deferred acquisition costs (37.0) (28.6)
Operating lease assets (13.7) (10.6)
Deferred Tax Liabilities, GAAP differences 0.2 8.3
Other temporary differences (6.4) (1.6)
Total deferred tax (liabilities) (57.3) (54.4)
Deferred tax assets, net $ 119.2  
Deferred tax liabilities, net   $ (2.8)